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676403

Sigma-Aldrich

(R,R)-(–)-2,3-Bis(tert-butylmethylphosphino)quinoxaline

≥95%

Synonym(s):

(R) QuinoxP®

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About This Item

Empirical Formula (Hill Notation):
C18H28N2P2
CAS Number:
866081-62-1
Molecular Weight:
334.38
MDL number:
MFCD10565649
UNSPSC Code:
12352005
PubChem Substance ID:
24884852
NACRES:
NA.22

assay

≥95%

form

solid

mp

100-104 °C

SMILES string

CP(c1nc2ccccc2nc1P(C)C(C)(C)C)C(C)(C)C

InChI

1S/C18H28N2P2/c1-17(2,3)21(7)15-16(22(8)18(4,5)6)20-14-12-10-9-11-13(14)19-15/h9-12H,1-8H3/t21-,22-/m0/s1

InChI key

DRZBLHZZDMCPGX-VXKWHMMOSA-N

Related Categories

General description

(R,R)-(-)-2,3-Bis(tert-butylmethylphosphino)quinoxaline is an air-stable C2-symmetric P-stereogenic phosphine ligand.

Application

Air-Stable and Highly Efficient Chiral Ligands
Efficient ligand exhibiting high levels of enantiocontrol in synthetic transformations ranging from metal-catalyzed 1,4-addition of arylboronic acids to alkylative ring opening to asymmetric hydrogenation.

Features and Benefits

Advantages of the QuinoxP* Ligands:
  • It is not oxidized nor epimerized at ambient conditions in air
  • Enantioselectivities are outstanding for various reaction paradigms
  • Hydrogenations proceed under mild reaction conditions
  • Low catalyst loadings yield high TONs

Citation

Fang P and Hou XL. "Asymmetric Copper-Catalyzed Propargylic Substitution Reaction of Propargylic Acetates with Enamines." Organic letters 11.20 (2009): 4612-4615.
Imamoto T, et al. "Highly enantioselective hydrosilylation of simple ketones catalyzed by rhodium complexes of P-chiral diphosphine ligands bearing tert-butylmethylphosphino groups." Tetrahedron: Asymmetry 17(4) (2006): 560-565.
Yahav-Levi A, et al. "Aryl-bromide reductive elimination from an isolated Pt (IV) complex." Chemical Communications 46(19) (2010): 3324-3326.

Legal Information

QuinoxP is a registered trademark of Nippon Chemical Industry Co., Ltd.

pictograms

Skull and crossbones
GHS06

signalword

Danger

Hazard Classifications

Acute Tox. 3 Oral - Aquatic Chronic 4 - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Faceshields, Gloves

Certificates of Analysis (COA)

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Asymmetric Copper-Catalyzed Propargylic Substitution Reaction of Propargylic Acetates with Enamines.
Fang P and Hou XL.
Organic Letters, 11.20, 4612-4615 (2009)
Highly enantioselective hydrosilylation of simple ketones catalyzed by rhodium complexes of P-chiral diphosphine ligands bearing tert-butylmethylphosphino groups.
Imamoto T, et al.
Tetrahedron Asymmetry, 17(4), 560-565 (2006)
A rational pre-catalyst design for bis-phosphine mono-oxide palladium catalyzed reactions.
Ji Y, et al.
Chemical Science (2017)
Tsuneo Imamoto et al.
Journal of the American Chemical Society, 127(34), 11934-11935 (2005-08-25)
A new P-chiral phosphine ligand, (R,R)-2,3-bis(tert-butylmethylphosphino)quinoxaline, has been prepared by the reaction of enantiomerically pure tert-butylmethylphosphine-borane with 2,3-dichloroquinoxaline. This ligand, in contrast to most of the previously reported P-chiral ligands, is an air-stable solid and exhibits excellent enantioselectivities in both
Aryl-bromide reductive elimination from an isolated Pt (IV) complex.
Yahav-Levi A, et al.
Chemical Communications (Cambridge, England), 46(19), 3324-3326 (2010)
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Articles

QuinoxP*

QuinoxP*: Air-Stable and Highly Efficient and Productive Chiral Ligands

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